Azo dyestuffs and process of making same



Patented June 1, 1926.

UNITED STATES PATENT OFFICE.

AUGUST LEOIPOLD SKA. AND :ABTHUB ZITSCHER, OF OFFENBACH-ON-THE-MAIN,

GERMANY, ASSIGINORS TO CORPORATION 'CHEMISGHE FABRIK GRIESHEIM-ELEKTRON', OI" FBANKFORT-ON-THE-HADT, GERMANY.

' AZO DYESTUFFS AND PROCESS OF MAKING SAME.

No Drawing. Application filed March 31, 1925, Serial No. 19,736, and inGermany Jnne 7, 1924.

The invention relates to new azo dyestufls groups, provided that and aprocess of making same, said dyestufi's 1s a halogen atom. havingprobably the general formula: The new dyestufls may be obtained by atleast one substituent submment combining any a-nilin-derivative,substituted in the 2 and 5--positions to the aminogroup N=N t 5 4 andcontaining in these positions at least one 2 3 halogen atom, such as l-chloro-1.2-toluidin, ubsmmmt 4-chloro-L3-toluidin, 4-chloro-L2-anisidin, 4-chloro-L3-anisid1n and the corresponding" phenetidins,2.5-dichloroanilin, 4-chloro-2- amino-diphenylether, with B-naphthalidof 2.3-hydro xynaphthoic acid. Especially'valu- H N formula:

ubstltuent wherein at least one substituent is a halo en atom, which arewhen dry yellowish re to on claret-red powders soluble in sulfur-1c acidto a violet solution, yielding u on reduct on with stannous chloride anan1lin-derivat1ve CO NH of the formula:

Substituent B 5 NH 1 4 ubstltuent hth lid f 1- i -2-h d whi h may beobtained by combining ambuiiiightlialer ie-3 carboxylic acid, adaptedfor derwatlles 0f the f rmula; the production of valuable color lakeswhen mixed with the usual substrate, and yleldlng when produced on thefiber, dyeln s, distinguished by clearness of shade an excellentfastness, particularly to kler-bolhn Under the name substituent 1n the ave mentioned formula we include substltuents such as halogens, alkyl-,O-alkyL,- 0 -ar,yl

7 B 5 NH 1 4 ubstituent able are the dyestufls having the general Thefollowing examples illustrate the in-" vention, the parts being byweight and all temperatures in Centigrade degrees.

Example 1.

caustic soda solution of 36 B. and 500 parts of water, and mixed withaquantity of sodium acetate which is necessary to combine with theexcess of the mineral acid in the diazo solution. When the combinationis complete, the precipitate is filtered oil. The dyestufi, havingprobably the formule:

is when dry a brilliant red powder soluble in concentrated sulfuric acidto a reddish violet solution and precipitated therefrom with water inred flakes. For the production of color lakes it is mixed, preferably inthe form of a nets, with the substrata usual for the pro notion of colorlakes and gives bluish red lakes of an excellent fastness.

Example 2.

Cotton yarn, which has been well boiled and dried, is impregnated with asolution of 3 r. of ,G-naphthalid of- 2.3-hydroxyliillfiltllOlC acid, 9cc. of caustic soda solution of 34 B. and 8 cc. of Turkey red oil perliter, well wrung out and, without bemg dried, developed, with adiazosolution, neutralized with chalk and containing 2.9 gr. of4-chloro-L2-toluidin or 4.4 gr. of 4-chloro- Q-amino-diphenylether, perliter, rinsed and soaped.

In this manner with both aminobases clear red shades of a very goodfastness to kier-boiling are obtained.

' T he new dyestulfsinay also be produced by the printing processaccording to one of the usual methods.

With other corresponding halogenated aminobases the process may beconducted in a similar manner. 1

Now what we claim and desire to secure by Letters Patent isthe'fol-lowing 1. As new compounds the azodyestutls, having probably thegeneral formula:

. Substituen Qubstituent wherein at least one substituent is a halogenatom, which are when dry yellowish red to claret-red powders, soluble insulfuric acid to a violet solution, yielding u on reduction withstannous chloride an anl in-derivative of the formula:

Substituent ubstituent and ,B-naphthalid of1-a1nino-2-hydroxynaphthalene-3-carboxylic acid, adapted, when mixedwith the usual substrate, for the production of valuable color lakes andyielding, when produced on the fiber, dyeings, which are distinguishedby clearncss of shadeand excellent fastness, particularly tokier-boiling.

2. The process of making new azodyestuffs consisting in combining anydiazotized anilin-derivative, substituted in 2 and 5 positions to theaminogroup and containing at least one halogen atom in these positions,with acid. I

3. Materials dyed with the new azodyestulis of claim 1, said dyestufi'sbeing produced on the fiber of the material.

B-naphthalid of 2.3-hydroxynaphthoic' 4.-As new compounds theazodyestufi's having probably the general formula:

ubstituent which are when dry yellowish red to claretred powders,soluble in sulfuric acid to a violet solution, yielding upon reductionwith stannous chloride an anilin-derivative of the formula;

ubstituent and B-naphthalid of 1-amino-2-hydroxynaphthalene-l-carboxylicacid, adapted, when mixed with the usual substrata; for the productionof Valuable color lakes and yielding, when produced on'the fiber,dyeings, which are distinguished by clearness of shade and'excellentpfastness, particularly to kier-b0iling.

5. The process of making new azodyestufis consisting in combining anydiazotized anilin-deri-vative of the formula:

2 a r ubstituenfi wiigl ,B- naphthalid of 2.3-hydroxynaphthoic aci i 6.Materials dyed with the new azodyestuffs of claim 4, said dyestuffsbeing produced on the fiber of material.

7. As a new compound the azodyestufi having probably the formula:

which is whendry a red powder soluble in sulfuric acid to a reddish"violet solution,

'stuif, consisting in combining diazotized 4- chloro-1.2-toluidinwithfl-naphthalid of 2.3- hydroxynaphthoic acid. i v

9. Materials dyed with the new dyestu'fi' of claim 7, saiddyestufiibeingproduced on the fiber of the material.

In' testimony,- that we claim the foregoing as our invention, we havesigned our names,

this 18th day of March 1925.

AUGUST LEoPoLD LASKA. ARTHUR zrrsoneqn.

